CN102108053B - Blue fluorescence compound and organic electroluminescence device using the same - Google Patents

Blue fluorescence compound and organic electroluminescence device using the same Download PDF

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CN102108053B
CN102108053B CN201010233451.1A CN201010233451A CN102108053B CN 102108053 B CN102108053 B CN 102108053B CN 201010233451 A CN201010233451 A CN 201010233451A CN 102108053 B CN102108053 B CN 102108053B
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electroluminescence device
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CN102108053A (en
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宾钟官
车淳旭
李昇宰
金重根
朴春键
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LG Display Co Ltd
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Abstract

The present invention relates to one and can obtain high brightness, long lifetime and high efficiency blue-fluorescence compound; And use its organic electroluminescence device.Described blue-fluorescence compound is made up of following Chemical formula 1.[Chemical formula 1] wherein, R1, R2 and R3 can be identical material or can not be identical material, and each R1, R2 and R3 are all independently for being selected from the one in the material of aryl, heterocyclic radical, fatty group and hydrogen.

Description

Blue-fluorescence compound and use the organic electroluminescence device of this blue-fluorescence compound
the cross reference of related application
The application requires the rights and interests of the korean patent application No.10-2009-0132606 submitting on December 29th, 2009, is incorporated in the application as a reference, as all recorded at this.
Technical field
The present invention relates to a kind of blue-fluorescence compound and a kind of organic electroluminescence device, relate more specifically to one and can obtain high brightness, long lifetime and high efficiency blue-fluorescence compound; And a kind of organic electroluminescence device that uses this blue-fluorescence compound.
Background technology
As the core technology in information communication epoch, the image display device that shows different information with picture is towards thinner, lighter and high-performance and portable future development.
Along with the various forms of demands of display device are increased and the development of informationized society recently, carrying out positive research for the flat-panel display device of such as LCD (liquid-crystal display), PDP (plasma display), ELD (electroluminescent display) etc.
In flat-panel display device, when in organic electro luminescent layer charge injection being formed between electron injection electrode (negative electrode) and hole injecting electrode (anode), form right electronics and hole and bury in oblivion, organic electroluminescence device is thereupon luminous.
Organic electroluminescence device not only can be formed in the flexible transparent substrate such as plastics, and can, by being driven lower than the voltage of Plasmia indicating panel or inorganic electroluminescence device, have relatively low watt consumption and fabulous color sensation.
Organic electroluminescence device can send redness, green or blue light according to the organic compound being included in electroluminescence layer.As this organic compound, be known that wherein aryl is substituted 2 at one end place of diphenylanthrancene structure, 2-(diaryl) vinyl phosphonic (2,2-(diarlyl) vinylphosphine) compound etc.
But because these the known organic compound including above-claimed cpd do not have enough life-spans, luminous efficiency and brightness, and blue purity is very poor, makes to be difficult to the blueness that provides pure, thereby be difficult to provide the panchromatic demonstration of natural light.
Summary of the invention
Therefore, the present invention is devoted to provide a kind of blue-fluorescence compound and a kind of organic electroluminescence device that uses this blue-fluorescence compound.
One object of the present invention is to provide a kind of blue-fluorescence compound and a kind of organic electroluminescence device that uses it, and this blue-fluorescence compound can obtain high brightness, long lifetime and high-level efficiency.
Additional advantages of the present invention, object and feature can partly be elaborated in the following description, and can in the time that those skilled in the art study following content, become clearly visible or can be obtained from the practice of the present invention.Object of the present invention and other advantage can be realized and be reached by the structure of specifically noting in written explanation and claim and accompanying drawing.
In order to obtain these objects and other advantage and according to object of the present invention, as embodied in this application and extensively describing, a kind of blue-fluorescence compound is made up of following Chemical formula 1.
[Chemical formula 1]
Figure BSA00000203473700021
Wherein, R1, R2 and R3 can be identical material or can not be identical material, and each R1, R2 and R3 are all independently for being selected from one of material of aryl, heterocyclic radical, fatty group and hydrogen.
The organic electroluminescence device of blue-fluorescence compound of the present invention has an electroluminescence layer between negative electrode and anode, and this electroluminescence layer comprises dopant species and main substance, and wherein, described dopant species has Chemical formula 1.
Each R1, R2 and R3 are all independently for being selected from one of xenyl, naphthyl, phenanthrene, terphenyl, pyridine, quinoline, deuterium and substituent material thereof.
Described aryl is the aromatic compound with alkyl, alkoxyl group, halogen, cyano group or silyl.
Described alkyl is the one being selected from methyl, ethyl, propyl group, sec.-propyl and the tertiary butyl, described alkoxyl group is the one being selected from methoxyl group, oxyethyl group and butoxy, described halogen group is the one being selected from fluorine and chlorine, and described silyl is trimethyl silyl.
Described organic electroluminescence device also comprises the hole injection layer and the hole transmission layer that are formed on continuously between anode and electroluminescence layer, and is formed on continuously electron transfer layer and electron injecting layer between electroluminescence layer and negative electrode.
Therefore, the organic electroluminescence device of blue-fluorescence compound of the present invention can drive under low voltage, and can improve purity, life-span and luminous efficiency.
Should be appreciated that aforementioned general remark of the present invention and following detailed description are all exemplary and explanatory, and be intended to provide the further explanation to claimed invention.
Brief description of the drawings
Be intended to provide a further understanding of the present invention and be incorporated to the accompanying drawing of a part that forms the application illustrate the application's embodiment and be used from specification sheets one principle of explaining the application.In the accompanying drawings:
Fig. 1 shows the schematic diagram of organic electroluminescence device according to the preferred embodiment of the present invention.
Embodiment
Below refer in detail to the specific embodiment of the present invention, embodiment is shown in the drawings.As possible, in institute's drawings attached, refer to same or similar parts with identical label.
Blue-fluorescence compound of the present invention has following Chemical formula 1.
[Chemical formula 1]
Figure BSA00000203473700041
Wherein, each R1, R2 and R3 all independently for replace or material non-substituted, that be selected from aryl, heterocyclic radical, fatty group and hydrogen in one.R1, R2 and R3 can be identical materials or can not be identical material.
Particularly, each R1, R2 and R3 all can be the one in the material that is selected from the group of the fragrance including phenyl, xenyl, naphthyl, phenanthrene, terphenyl, pyridine, quinoline, deuterium and substituting group thereof.
Or, each R1, R2 and R3 all can be selected from there is alkyl, one in the material of the aromatic compound of alkoxyl group, halogen, cyano group and silyl.
Described alkyl is the one being selected from methyl, ethyl, propyl group, sec.-propyl and t-butyl, and described alkoxyl group is the one being selected from methoxyl group, oxyethyl group and butoxy.Described halogen group is the one being selected from fluorine and chlorine, and described silyl is trimethyl silyl.
Particularly, the compound of Chemical formula 1 can be the compound with following chemical formula BD-1 to BD-360.But the compound of Chemical formula 1 is not limited to these compounds.
Figure BSA00000203473700051
Figure BSA00000203473700061
Figure BSA00000203473700071
Figure BSA00000203473700081
Figure BSA00000203473700091
Figure BSA00000203473700101
Figure BSA00000203473700111
Figure BSA00000203473700121
Figure BSA00000203473700131
Figure BSA00000203473700141
Figure BSA00000203473700151
Figure BSA00000203473700161
Figure BSA00000203473700171
Figure BSA00000203473700181
Figure BSA00000203473700201
Figure BSA00000203473700211
Figure BSA00000203473700221
Figure BSA00000203473700231
Figure BSA00000203473700241
Figure BSA00000203473700251
Figure BSA00000203473700261
Figure BSA00000203473700271
Figure BSA00000203473700281
Figure BSA00000203473700291
Figure BSA00000203473700301
Figure BSA00000203473700311
Figure BSA00000203473700321
Figure BSA00000203473700331
Figure BSA00000203473700341
Figure BSA00000203473700351
Figure BSA00000203473700361
Figure BSA00000203473700371
Figure BSA00000203473700381
Figure BSA00000203473700391
Figure BSA00000203473700401
Figure BSA00000203473700411
Figure BSA00000203473700431
Figure BSA00000203473700441
Below adopt the compound in blue-fluorescence compound of the present invention with chemical formula BD-10 to describe a kind of method for the preparation of blue-fluorescence compound of the present invention.
[synthetic example]
1) synthetic N-phenyl-3,5-phenylbenzene aniline
Figure BSA00000203473700442
In round-bottomed flask, by aniline (3g, 10.75mmol), m-terphenyl (3.34g, 10.85mmol), Pd 2(dba) 3(3mol%) and t-BuONa (1.45g, 15.05mmol) be dissolved in toluene, at 100 DEG C, stir this solution.In the time completing its reaction, from this solution, remove toluene, and by making water and methylene dichloride extract compound from solution.By separate the compound that extraction obtains thus with silica gel.By carry out this material separating of recrystallization with methylene dichloride and sherwood oil, and filter, obtain N-phenyl-3,5-phenylbenzene aniline (2.9g, 84%).
2) prepare 1,6 two (N-phenyl-N-(m)-terphenyl) pyrene
Figure BSA00000203473700451
In round-bottomed flask, by 1,6 dibromo pyrene (1g, 2.78mmol), N-phenyl-3,5-phenylbenzene aniline (1.87g, 5.83mmol), Pd 2(dba) 3(3mol%), BINAP (4mol%) and t-BuONa (0.78g, 8.16mmol) be dissolved in toluene, stirs this solution at 100 DEG C.In the time completing its reaction, from this solution, remove toluene, and by making water and methylene dichloride extract compound from solution.By separate the compound that extraction obtains thus with silica gel.By carry out this material separating of recrystallization with methylene dichloride and sherwood oil, and filter, obtain 1,6 two (N-phenyl-N-(m)-terphenyl) pyrene (BD-10; 4.27g, 87%).
With reference to Fig. 1, the organic electroluminescence device 130 of blue-fluorescence compound of the present invention comprise anode 132, negative electrode 138 and be formed on anode 132 and negative electrode 138 between and there is the electroluminescence layer of main substance and dopant species.Dopant species in this electroluminescence layer has following Chemical formula 1.
[Chemical formula 1]
Figure BSA00000203473700461
Wherein, each R1, R2 and R3 are all independently for being selected from one of material of aryl, heterocyclic radical, fatty group and hydrogen, and it is replacement or unsubstituted.Described R1, R2 and R3 can be identical material or can not be identical material.
Particularly, R1, R2 and R3 can be the one in the material that is selected from the aryl including phenyl, xenyl, naphthyl, phenanthrene, terphenyl, pyridine, quinoline, deuterium or its substituting group.
Or each R1, R2 and R3 can have alkyl for being selected from, one in the material of the aromatic compound of alkoxyl group, halogen, cyano group and silyl.
Described alkyl is the one being selected from methyl, propyl group, sec.-propyl and t-butyl, and described alkoxyl group is the one being selected from methoxyl group, oxyethyl group and butoxy.Described halogen group is the one in fluorine and chlorine, and described silyl can be trimethyl silyl.
Particularly, the dopant species in electroluminescence layer 135 can be for having the one in the compound of following chemical formula BD-1 to BD-360.But dopant species is not limited to those.The main substance of coming together to form electroluminescence layer with the dopant species that is selected from BD-1 to BD-360 can be 4,4 '-bis-(2,2-hexichol)-1,1 ' biphenyl (4,4 '-bis-(2,2-diphenylacetylene)-1,1 '-biphenyl (4,4 '-bis (2,2-diphenyl)-1, and 1 ' biphenyl (4,4 '-bis (2,2-diphenylvinyl)-1,1 '-biphenyl; DPVBi).But described main substance is not limited to those, but can use any known material.
[Chemical formula 2]
Figure BSA00000203473700471
In addition, organic electroluminescence device 130 can comprise hole injection layer HIL133 and the hole transmission layer HTL134 between anode 132 and electroluminescence layer 135, or electron transfer layer ETL136 and electron injecting layer EIL137 between electroluminescence layer 135 and negative electrode 138.
Anode 132 can be formed by ITO (tin indium oxide) conventionally, and hole injection layer 133 can mainly be formed by the copper phthalocyanine CuPc with following chemical formula 3.
[chemical formula 3]
Figure BSA00000203473700472
Hole transmission layer 134 can be formed by 4,4 '-bis-[N-(1-naphthyl)-N-phenyl amino]-biphenyl NPB with following chemical formula 4.But the material of hole transmission layer 134 is not limited to this, but can be any known hole transport material.
[chemical formula 4]
Figure BSA00000203473700481
Electron transfer layer 136 can (for example have three (8-hydroxyl yl-quinoline) aluminium Alq of following chemical formula 5 by 8-hydroxyl yl-quinoline 3) institute form.But the material of electron transfer layer 136 is not limited to this, but can be any known electric transmission material.
[chemical formula 5]
Figure BSA00000203473700482
Electron injecting layer 137 can be formed by LiF.But the material of electron injecting layer 137 is not limited to this, but can be any known electronic injection material.Negative electrode 138 can be formed by any known metal.
By the blue-fluorescence compound that is selected from BD-1 to BD-360 is used as to the dopant species in the electroluminescence layer 135 of organic electronic light emitting device 130, the present invention can obtain has the very blue-fluorescence organic electroluminescence device of high-luminous-efficiency, excellent heat resistance, long lifetime and high color purity.
A kind of for the preparation of having in the method for organic electroluminescence device of blue fluorescent substance of the present invention, on substrate, form anode, on anode, form continuously hole injection layer, hole transmission layer, electroluminescence layer, electron transfer layer and electron injecting layer, form afterwards negative electrode.In this case, described electroluminescence layer comprises main substance and dopant species.The dopant species of described electroluminescence layer can, for having the compound of above-mentioned Chemical formula 1, particularly, can be a kind of compound being selected from compd B D-1 to BD-360.
Described main substance can be the DPVBi with above-mentioned Chemical formula 2, and described hole injection layer can be formed by the CuPC with above-mentioned chemical formula 3.Described hole transmission layer can be formed by the NPB with above-mentioned chemical formula 4, and described electron transfer layer can be by the Alq with above-mentioned chemical formula 5 3institute forms, and described electron injecting layer can be formed by LiF.Described negative electrode can be by being formed such as the known metal of aluminium A1.
But, the material of hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer is not limited to above-mentioned materials, but can be any known hole injection layer material, any known hole transmission layer material, any known electron transfer layer material and any known electron injecting layer material.
In the method for the manufacture of organic electroluminescence device, by the blue-fluorescence compound that is selected from BD-1 to BD-360 is used as to dopant species, the present invention can obtain a kind of blue-fluorescence organic electroluminescence device with high-luminous-efficiency, excellent heat resistance, long lifetime and high color purity.
A kind of multiple embodiments of method of organic electroluminescence device for the manufacture of having blue-fluorescence compound of the present invention are below described.But the present invention is not limited to following these embodiments.
[embodiment 1]
An ito glass is carried out to composition to have the light-emitting zone of 3mm x 3mm size, after cleaning, form substrate.In substrate is arranged on to vacuum chamber and to vacuum chamber, find time to there is 1x10 -6after the basic pressure of torr, by organic substance according to
Figure BSA00000203473700491
main body
Figure BSA00000203473700492
+ doping agent BD-4 (5%),
Figure BSA00000203473700493
and
Figure BSA00000203473700494
sequential applications on ITO, to make organic electroluminescence device.The 616cd/m when organic electroluminescence device of making thus demonstrates 0.9mA 2(5.82V) and CIE x=0.143, y=0.101.
[embodiment 2]
An ito glass is carried out to composition to have the light-emitting zone of 3mm x 3mm size, after cleaning, form substrate.In substrate is arranged on to vacuum chamber and to vacuum chamber, find time to there is 1x10 -6after the basic pressure of torr, by organic substance according to
Figure BSA00000203473700495
main body
Figure BSA00000203473700496
+ doping agent BD-18 (5%), and
Figure BSA00000203473700498
sequential applications on ITO, to make organic electroluminescence device.The 682cd/m when organic electroluminescence device of making thus demonstrates 0.9mA 2(6.03V) and CIE x=0.146, y=0.110.
[embodiment 3]
An ito glass is carried out to composition to have the light-emitting zone of 3mm x 3mm size, after cleaning, form substrate.In substrate is arranged on to vacuum chamber and to vacuum chamber, find time to there is 1x10 -6after the basic pressure of torr, by organic substance according to
Figure BSA00000203473700501
main body
Figure BSA00000203473700502
+ doping agent BD-24 (5%),
Figure BSA00000203473700503
and
Figure BSA00000203473700504
sequential applications on ITO, to make organic electroluminescence device.The 623cd/m when organic electroluminescence device of making thus demonstrates 0.9mA 2(5.95V) and CIE x=0.143, y=0.098.
[embodiment 4]
An ito glass is carried out to composition to have the light-emitting zone of 3mm x 3mm size, after cleaning, form substrate.In substrate is arranged on to vacuum chamber and to vacuum chamber, find time to there is 1x10 -6after the basic pressure of torr, by organic substance according to
Figure BSA00000203473700505
main body
Figure BSA00000203473700506
+ doping agent BD-77 (5%),
Figure BSA00000203473700507
and sequential applications on ITO, to make organic electroluminescence device.The 595cd/m when organic electroluminescence device of making thus demonstrates 0.9mA 2(6.11V) and CIE x=0.140, y=0.088.
[embodiment 5]
An ito glass is carried out to composition to have the light-emitting zone of 3mm x 3mm size, after cleaning, form substrate.In substrate is arranged on to vacuum chamber and to vacuum chamber, carry out exhaust to there is 1x10 -6after the basic pressure of torr, by organic substance according to
Figure BSA00000203473700509
main body
Figure BSA000002034737005010
+ dopant BD-134 (5%),
Figure BSA000002034737005011
and sequential applications on ITO, to make organic electroluminescence device.The 576cd/m when organic electroluminescence device of making thus demonstrates 0.9mA 2(5.93V) and CIE x=0.139, y=0.084.
[comparing embodiment 1]
An ito glass is carried out to composition to have the light-emitting zone of 3mm x 3mm size, after cleaning, form substrate.In substrate is arranged on to vacuum chamber and to vacuum chamber, carry out exhaust to there is 1x10 -6after the basic pressure of torr, by organic substance according to
Figure BSA000002034737005013
main body
Figure BSA000002034737005014
+ doping agent BD-a (1%),
Figure BSA000002034737005015
and sequential applications on ITO, to make organic electroluminescence device.The 526cd/m when organic electroluminescence device of making thus demonstrates 0.9mA 2(6.7V) and CIE x=0.136, y=0.188.
The results are shown in following table 1 of embodiment 1 to 5 and comparing embodiment 1.
[table 1]
Device Voltage (V) Electric current (mA) Brightness (cd/m 2) CIE(x) CIE(Y)
Embodiment 1 5.82 0.9 616 0.143 0.101
Embodiment 2 6.03 0.9 682 0.146 0.110
Embodiment 3 5.95 0.9 623 0.143 0.098
Embodiment 4 6.11 0.9 595 0.140 0.088
Embodiment 5 5.93 0.9 576 0.139 0.084
Comparing embodiment 1 6.7 0.9 526 0.136 0.188
As shown in above-mentioned embodiment, we are known is selected from the compound of BD-1 to B-360 as the dopant species of electroluminescence layer of the present invention by introducing, described organic luminescent device can be driven under the voltage 0.59V～0.88V of the dopant species lower than prior art, and has the lower CIE coordinate that can improve purity of color.In addition the organic electroluminescence device that, has a blue organic fluorescent compounds of the present invention can have very high luminous efficiency and very long luminescent lifetime.
Those skilled in the art can know clearly, without departing from the spirit and scope of the present invention in the situation that, can make various amendments and distortion to the present invention.Therefore,, if these amendments and distortion are in the scope of claims and Equivalent thereof, this invention is intended to cover these amendments of the present invention and distortion.

Claims (3)

1. a blue-fluorescence compound, for being selected from a kind of compound in following compounds,
Figure FDA0000459393020000011
2. blue-fluorescence compound has an electroluminescent device, has the electroluminescence layer between negative electrode and anode, and described electroluminescence layer comprises dopant species and main substance,
Wherein, described dopant species is for being selected from compound claimed in claim 1.
3. device according to claim 2, wherein, also comprise hole injection layer and the hole transmission layer being formed on continuously between described anode and described electroluminescent device and be formed on continuously described electroluminescence layer and described negative electrode between electron transfer layer and electron injecting layer.
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